


One Bad Line

by okeypokeysmokey



Category: Supernatural
Genre: Awkwardness, Frottage, Hand Jobs, M/M, Oral Sex, Pickup Lines, Smut
Language: English
Status: Completed
Published: 2013-02-27
Updated: 2013-02-27
Packaged: 2017-12-03 18:48:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,628
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/701478
Author URL: https://archiveofourown.org/users/okeypokeysmokey/pseuds/okeypokeysmokey
Summary: <blockquote class="userstuff">
              <p>Dean uses one bad line after a few beers and starts a chain of events.</p>
            </blockquote>





	One Bad Line

The three boys were sitting in their undersized motel room, each holding a half emptied bottle of beer. They had just finished a particularly nasty hunt and were celebrating a bit before hitting the road once more. Sam was sitting comfortably at the tiny two-person table by the window and Dean was perched at the end of one of the two crappy motel beds, slouching lazily. Castiel had found a nice spot on the counter of the tiny kitchen area, his back facing into the cozy crook of the corner with his elbows resting on his knees. Dean’s eyes fell on Cas, they seemed to do that quite a bit these days, more than Dean would like to admit. Lately he’d been thinking about giving in to the part of him that caused all the lingering looks, it’s not like he could control who he... grew attached to. He was only human after all, and not a very good example of one ether; at least that’s what Dean thought. Cas’ eyes met with Dean’s and the Angel’s expression changed in that subtle way that just made it seem so Cas. If Dean didn’t have better control of his expressions, he would have smiled.   
“Is something wrong, Dean?” said Castiel in that wonderfully raspy voice the Winchester boys had come to know so well. This time Dean did smile, just a bit. A little boyish half smile with a hint of wry humor. Well, why the hell not. He’d had just enough alcohol to make it seem like a case of tipsy-tongue, and he knew the perfect line too. Dean never thought he’d say this, but he couldn’t pass up the opportunity.   
“Nah, I’m alright.” Dean said with sly undertone. “I was just wondering if it hurt.” Sam looked at his brother with disbelief, his eyebrows raised high as if to say ‘Really, Dean? This is what you come out with?’ Cas just looked more confused, and maybe slightly concerned.   
“Did what hurt?” said the Angel, doing a quick sweep of his body to make sure he didn’t have any wounds. Dean looked down for just a second and then looked back up at Cas from under his long lashes.   
“When you fell from Heaven?” Dean said, dropping his voice a few notches to make the question sound more sensual. Sam rolled his eyes and shook his head, trying hard not to laugh. Cas gave Dean that look that questioned the older Winchester’s sanity.   
“I was already on Earth when I rebelled, Dean; ‘fall’ is mostly used theoretically in this context.” said Castiel in a very matter-of-fact sort of tone. Dean huffed out a short, breathy chuckle while Sammy burst in to thunderous rounds of laughter. Cas looked between the brothers. Surly they must have gone mad, or were they already drunk?   
“Have I missed something important?” Castiel asked hesitantly, which brought on an especially loud throng of laughter from the younger Winchester.   
“Shut up.” Dean said to his brother in a slightly humiliated tone. He’d expected it to go this way, but it still stung a bit. The half-hearted command just made Sam laugh harder which made Dean shake his head and give a small, resigned smile. He knew he deserved it for saying something stupid like that, and to Castiel nonetheless. He took another swig from his bottle, he could always try again. Next time though, he’d use better lines.   
Cas looked between the two boys a couple more times and then gave in. He wrote it off as a weird human thing for the time being and took a sip from his own bottle. The Angel was sure he’d never understand humans.   
******************************************************************************************************************************************************************************  
The two Winchester boys were at a table in a diner, grabbing some lunch before running off to save the world from monsters and demons. Sam kept giving Dean amused looks, like he wanted to make some smart-ass comment. Dean had a feeling he knew what his brother wanted to bring up, so he avoided saying too much. Finally he couldn’t take it any longer; he put his utensils down and gave Sammy an exasperated look.   
“What?” He said with as much annoyance as he could muster up.   
“Nothing.” Sam said with humor bubbling in his voice. “No, I was just wondering if it hurt.” He said with a mocking smile.  
“Go to hell.” Dean said. He picked up his silverware again so he wouldn’t have to look at the little shit across from him. Sam chuckled at his brother’s expense; there was no way he was just going to let that slide.   
“What were you thinking?” Dean ignored the question. Sam tried to sound a bit more serious. “Really, I want to know.” Dean looked up at his brother again. Their eyes met and held for a while and a short, silent communication took place. Dean sighed in resignation. He rolled his eyes as he gave in – yet again – to the power of the puppy-dog eyes.   
“I wasn’t, okay? I was tipsy; it seemed like a good idea at the time.”   
“Oh come on, there had to be something running through your head.”  
Dean hesitated for a second; he figured that Sammy would have to find out sooner or later. He gave in. “Well, I guess I was thinking... ‘What the hell?’ it’s not like he’d get it anyways.” He said, trying his best to avoid eye contact at the last part. The wheels turned in Sam’s head; he’d noticed the way Dean had been looking at Cas lately, but he couldn’t figure out why. Dean’s poorly hidden bashfulness finally made it click.   
“Wait, do you actually...?” Dean’s eye’s flicked up to Sam’s for less than a second and then they were trying their best to look at everything else – anything else. That was confirmation enough. “Ok.” He paused for a second, letting it sink in. “So are you...” He didn’t quite know how to finish the sentence.   
“Am I what?” Dean said, covering his embarrassment with annoyance.   
“I don’t know! I mean, are you going to, like... try again? Keep flirting or... whatever that was?” Sam said, being serious but also trying to bring humor back into the conversation. Dean huffed out a little half-laugh. He’d been rethinking his earlier intentions.   
“Ah... I don’t know.”  
“What? Come on, if you’re serious about this then you can’t just try once and give up.” Dean looked up at his pain of a brother again. They locked eyes for a few seconds and then Dean looked away, the implication was clear.   
“Come on! Okay, I dare you to try again.” Dean’s gaze snapped back up, his eye brows high.   
“Really Sam?”  
Sam smirked. “I double dare you.”   
They stared each other down for a long time. Dean knew that if he backed down from this not only would Sam be calling him a pussy for the next week, but he’d also tease him about Cas every chance he got. He drew a deep breath and released a slow, long-suffering sigh.   
“Fine, but only because I don’t want to listen to your smart-ass comments.”   
Sam smiled in triumph. With Dean exasperated and Sam satisfied the boys went back to their meals. As they were finishing up, a familiar figure appeared at the table. The boys jumped a bit at the sudden appearance, it was a thing you just don’t get used to. Sam flashed Dean a meaningful look before focusing on the Angel in the room.   
“What have you got?” Castiel asked, getting right to the point as usual.   
“Well-” Sam started to explain the newest case but was cut off by the waitress.  
“All done, boys?” She said in the forced pleasantness of a teenager at a summer job.  
“Yes, thank you.” Said Dean as the girl took the emptied plates.   
“Can I interest you in any deserts? We have some great key-lime pie.” She said in an unconvincing tone.   
“Nah, we’re good for today.” Dean smiled politely and the waitress nodded and walked away with the dishes balanced on her arm. Sam gave Dean a look of surprise.   
“You don’t want desert?”   
“Nah, I already have a nice piece of Angel Cake right here.” He said, nodding in Cas’ direction. Castiel looked at Dean questioningly and Dean met the Angel’s gaze with a quick wink. He then stood up and grabbed his coat. “C’mon, we can talk on the road.”   
Sam chuckled and stood as well, grabbing his coat and pulling it on. Cas never took his gaze off of Dean as the older Winchester strode out the door, what was that? Sam placed a hand on Castiel’s shoulder to shake the Angel out of his trance.   
“C’mon, Angel boy” Sam said, amusement written all over his face as he followed Dean out the door. Cas didn’t bother getting up; he instead took a minute to think about what Dean had said. Was Dean trying to be ‘flirty’? No, that couldn’t be right; Dean was probably just ‘messing with him’. A part of Cas would have liked to think that Dean was ‘flirting’ with him, but that part was small and fairly easy to ignore. With his conclusion, Castiel appeared in the back seat of the Impala.   
The Winchester boys jumped once again as the Angel appeared out of nowhere. Dean rolled his eyes. “Glad you could make it, sunshine.” Dean said sarcastically.   
“You knew I was coming.” Cas said in that clueless tone. Dean chuckled and shook his head as he started the engine. He tried not to think about his ‘little stunt’ in the diner and how his heart was still racing from it. He shifted the gear into drive and ten minutes later the boys were speeding down the highway.   
******************************************************************************************************************************************************************************  
Castiel appeared in the back seat of the Impala. Sam was in the building to the right of the car getting some important things for the newest investigation. Dean however, was still in the car; Dean was singing to a song that Cas didn’t recognise. The song didn’t sound like something Dean would normally listen to. The Angel decided not to say anything just yet.   
“...old me near, you drown out the cro-oowd... Old Mr. Webster could never define, what’s bein’ said between your heart and miiine. The smile on your face lets me know that you need me. There’s a truth in your eyes, saying you’ll never leave me the touch of your hand, says you’ll catch me. If ever I faaaaall... you say it best. when you say nothing a- CAS!” Dean exclaimed, finally realizing the Angel’s presence. He quickly turned off the stereo and removed the tape from its compartment. The label was blank and Cas suspected there was only the one song on it. The Angel’s eyes met Dean’s embarrassed expression; the two held each-other’s gaze for a few seconds until Castiel decided to break the silence.   
“What was-”  
“It’s a guilty pleasure!” Dean said defensively; he was clearly humiliated by the situation. He looked away from Cas to put the tape back in the very back of the glove compartment.   
“I don’t think I’m familiar with that term.” Cas said with a bit of curiosity in his voice. As strange as he found human terms and sayings, he liked some of them and thought they could be useful if he ever remembered to use them.   
“It’s something you like, but are embarrassed about or something you feel guilty for liking. For example, a nineteen-year-old might feel guilty for dating a sixteen-year-old because it’s technically illegal. Or maybe a Fashionista might have a really big, frumpy sweater that they really liked, that’s something they would call a guilty pleasure.”   
“I see. So because it was a very sweet song-”  
“Yes.” Dean said in a clipped tone, he wanted to avoid too much discussion about his song choice. “I’ve been trying to get rid of it for so long, but I just can’t bring myself to finally get rid of the tape. Every time I try I just end up listening to the damn thing again.” He said, letting out a frustrated sigh. Cas thought for a minute.   
“Maybe you should try to find a different ‘guilty pleasure’?”   
Dean was about to say something sarcastic, but then he saw a great opportunity.   
“That’s actually not a bad idea.” Dean said as he turned to look the Angel in the eye. “In fact, I think I already found one.” He said sensually, his eyes full of meaning.   
“That’s good, is it better than the other one?” Cas asked, completely missing the implication.   
Dean looked away from his Angel, disappointed that the other hadn’t understood. Before anything more could be said, the passenger door opened and Sam climbed in with a shopping bag in each hand.   
“Got ‘em.” He said, gesturing to the bags in his lap.”   
“Alright, let’s get this party started.” And with that, Dean started up the engine and the boys were on their way back to the motel to prepare for the night’s events.   
Dean would later stand by the trash bin for a long minute with the tape in his hand. After a lot of thought, he would let the tape slip from his hand and into the pail below. He would then leave the room without looking back. Not even once.  
******************************************************************************************************************************************************************************  
Dean put the empty glass down on the table. The things he did for this job. Admittedly it wasn’t all bad, lots of hot men in skimpy outfits made for good scenery. The problem was the guy Dean was supposed to ‘butter up’. The guy was really not Dean’s type, a body-builder with an over flirty attitude. Dean was pulled out of his thoughts when a figure appeared at his table.   
“Have you located the target?” The Angel asked.   
Dan sighed reluctantly. “Yeah, he’s the muscle-freak in the back-left.” Dean waved his hand in the air to signal for the waiter to bring two more rounds.   
“Right. So how do we approach him?”   
“We don’t. You will stay here and I will approach him.” Dean said in a way that got the ‘no buts’ message across.   
“What will you do?”   
“You’d be surprised what people will admit to when they think someone’s interested in them.” Cas nodded as if he understood, but he had a blank look on his face that said otherwise. Dean rolled his eyes.   
“I’m going to flirt with him, Einstein.” Understanding flooded Cas’ eyes as it finally clicked. The drinks had just arrived and the Angel immediately took a swig.   
“Right.” Was all that came out of Castiel. The Angel didn’t really know what else to say about it. The two sat there in silence for a while as they drank the strong alcohol in their cups. Dean sighed when he finished his glass.   
“Alright, better get this show on the road.” Dean didn’t make a move to get up; he instead looked over at the aforementioned ‘muscle-freak’. His gaze sat there for a while before he turned away to wave down the waiter again. More drinks came and Dean still didn’t get up to ‘flirt’ with the target. The only thing that had changed was that every so often Dean would look at the man for a while and then return his attention to his drink. Castiel didn’t want to seem like an idiot again, but he couldn’t hold back his curiosity any longer.   
“Dean, what are you doing?” The Angel asked with real confusion in his voice.   
“Flirting is like a game of wits. I can’t just walk over there out of the blue; I have to make him know that I’m interested first.” Dean said while looking at the target. He seemed to have gained the man’s attention.   
There was a short pause while Cas digested this. There was something about that last bit the Angel didn’t like, but he couldn’t quite figure out what it was exactly. And then his mouth was moving of its own accord.   
“Are you interested?” Cas asked hesitantly. He was surprised at himself; where had that question come from? And more importantly, why did he care so much about the answer?   
Dean looked Castiel in the eye. “Honestly? Not at all. But he has to think I do.” Dean looked back at the target again. Their eyes met and Dean smiled and winked in the most charming way, or at least Cas thought it was charming. He had noticed that his view and the views of humans were very different at times. The target seemed to take the bait though, and Dean finally got up to talk to the muscle-man.   
Dean seemed to be very good at the process of seduction. He said all the right things in just the right ways; it was no wonder the target was putty in Dean’s hands after only five-or-so minutes. There was something about the situation the Angel didn’t like. He tried not to pay attention but no matter how hard he tried he kept focusing on the conversation across the room. It seemed to be going very well, but then there was a pause in the conversation. Cas looked over to see what the problem was. He turned just in time to see the target give Dean a deep kiss and a firm squeeze to the Winchester’s rear. The Angel looked away, confused by the rush of emotion that scene had caused. Cas recognized it as a type of envy, or at least this is how he was told it was supposed to feel. Another minute passed and then Dean was back in his place next to Cas. The Angel’s mouth was moving again.   
“Having fun?” Cas said with a virtually undetectable amount of bitterness in his tone, he’s at least been able to control that.  
“Go to Hell.” Dean said as he often did to his brother. It seemed that Dean thought Castiel was ‘teasing’ him. That was fine with Cas. “That was awful! He tasted like appletinis and fruity lip balm.” Dean complained while wiping his mouth. It pleased Cas that Dean had not enjoyed his encounter with the target. He realized how strange this was and wondered where this all was coming from. He could mull it over later, now there was business to handle.   
“What did you learn?”   
“Hold up, I’ll call Sam and get him on speaker phone.” Dean said as he pulled out his mobile. “Might as well tell you both at once.” The phone rang two and a half times before Sam picked up.   
“What’s up?”   
“Good news, I’ve got the location.”  
“Really?”  
“Yup, even got some extra info.”   
“Wow, how did you manage that?”  
“Well, let’s just say it involved lip balm and my ass being crushed.”   
“Oh, sorry man.” Sam was obviously holding back laughter.   
“Do you wanna know the details or not? I’m getting slammed as soon as I hang up and hopefully I won’t remember squat by morning.”  
“Alright, alright just tell me what you got.”  
Dean told the two boys everything he’d learned from the target. He ordered another round of drinks as soon as he hung up. Cas decided to stay with Dean for the night, he figured Dean would need a way home if ‘getting slammed’ meant what he thought it did.  
About an hour later, Dean showed all signs of being completely intoxicated. He was giggling and slurring and saying things he wouldn’t normally say out loud. Cas found it quite amusing. Dean turned his drunken gaze on the Angel and then started to stroke Castiel’s jaw line. He giggled lazily.   
“Yer face iz prickly.” Dean said with childish amusement. He went to take another sip of his drink but Cas stopped him.   
“Dean, I think you’ve had enough.”  
“Why?” Dean said in almost a whine  
“You’re drunk, you need to-“  
“What? I’m not drunk! I’m just intoxicated by you...” Dean drawled out as he swayed closer to Cas. The Angel’s neck grew a bit warmer from the statement; he cleared his throat before placing his hand on Dean’s shoulder.  
“Alright, time for bed.” At some point during that sentence, Cas had popped them back to the motel. Cas led Dean to the bed while the older Winchester slurred out half-hearted protests. When Cas finally got Dean down on the bed Dean looked up at the Angel with a dopey smile.   
“You shoulds sleep here with me t’night.” Dean said lazily.  
“I don’t sleep, Dean.”  
“Why nooot? Sleep is good.”   
“I’m an Angel, I don’t need to sleep.”  
“Angel-shmangel, cm’ere.” Dean said, patting the bed with a floppy hand. Cas decided to humor Dean; he walked to the opposite side of the bed and awkwardly laid down beside the older Winchester, facing towards him. Dean managed to turn over to look at Cas as well, lazy grin still plastered on his face. Cas smiled just a little bit at the big drunken dope in front of him.  
“Goodnight Dean.” Cas said with an undertone of insistence.  
Dean sighed contentedly. “G’night Angel Cake”  
Dean was asleep within minutes, snoring and occasionally mumbling. Cas stayed beside Dean most of the night, but decided that both Winchesters would be alarmed if he was still there when they woke up. When Dean did wake up he had a huge hangover and a limited memory of the previous night. They all decided that was for the best.   
******************************************************************************************************************************************************************************  
Cas was sitting in the Winchester’s motel room. Dean was on a ‘supply run’ and Sam was leafing through another lore book. Cas was thinking about the previous night, and about Dean. Specifically what Dean had said, did he mean it? Within a week the part of Cas that wanted Dean to have meant it – the part that used to be so easy to ignore – had grown considerably in size and was now part of the Angel’s regular thoughts. But what could Cas do? Dean didn’t remember much from the night before so Cas couldn’t just ask about it. Even if he could, he didn’t think he would. There was something in him that was keeping him from confronting Dean about this whole thing, but what? Fear? Shame? Fear of shame?   
“Hey Cas?” Sam asked, pulling the Angel out of his troubled thoughts.  
“Yes?”  
“What exactly happened last night?”   
“Why do you want to know?”   
Sam smiled sheepishly. “Well, whatever it was Dean didn’t sound happy about it. And he’s also really funny when he’s drunk.” Ah, it was for amusement. Cas decided to be compliant.   
“Well, when I got there Dean already had a plan about how to approach the target.” Of course Cas would start off factual. Sam was patient; he knew that the Angel would get to the good stuff soon. “The plan was to get the man to talk using seduction, although the man didn’t seem to be Dean’s ‘type’.”  
“What did he look like?”  
“Dean described him as a ‘muscle freak’. He also seemed... overly friendly I suppose.”   
Sam chuckled. “Oh.” More giggles. “I see. So then what happened?”  
“Dean decided to ‘get the show on the road’. I thought he meant that he was going to go talk to the target, but he just turned around and started looking at the target every so often. I asked him what he was doing and he explained to me how ‘flirting’ works.” Sam had to hold back a laugh at that. “Eventually Dean did get up and talk to the target, it must have gone well because – well you know how it ended.”   
Sam snorted a laugh and nodded. “The poor bastard.” He said with amusement, referring to his brother. “What about when he was drunk?”  
“There was a lot of giggling and ridiculous comments, but it wasn’t until he stroked my jaw and told me my face was ‘prickly’ that I decided he’d had enough.”  
“Woah, woah, woah, wait! He actually did that?”  
“Yes.”  
Sam chuckled and rubbed his hand over his face. Drunken Dean really was hilarious. “So what did you do?”  
“I tried to cut him off, but he said...” Cas trailed off, not sure if he should tell Sam about that bit, or if he wanted to.   
“He said what?” Sam asked, a little concerned by the lack of ending to the previous sentence.   
“Well-” The Angel was too bashful to say it himself, but it didn’t show in his expression. “Uh, I think it’s easier if I just show you.”   
“What do you mea-” Cas tapped Sam’s forehead and then Sam was at a bar, sitting beside a man with an ‘EL SOL’ tattoo. He looked around and spotted Dean, looking completely smashed. It seemed that no one here could see him or hear him; he figured that this must be what Cas meant by ‘show him’. He walked over to Dean and Cas’ table to see what was going on.   
“Yer face iz prickly.” Dean said with childish amusement. He went to take another sip of his drink but Cas stopped him.   
“Dean, I think you’ve had enough.”  
“Why?” Dean said in almost a whine  
“You’re drunk, you need to-“  
“What? I’m not drunk! I’m just intoxicated by you...” Dean drawled out as he swayed closer to Cas.  
Sam noticed the Angel stiffen up. If he didn’t know any better, he’s say that Cas was blushing.   
Cas cleared his throat awkwardly and then placed his hand on Dean’s shoulder.  
“Alright, time for bed.” At some point during that sentence, Cas had popped them back to the motel. Cas led Dean to the bed while the older Winchester slurred out half-hearted protests. When Cas finally got Dean down on the bed Dean looked up at the Angel with a dopey smile.  
The scene changed and Sam was back in the crappy motel room with Cas, who had decided it was for the best to leave out the part about sleeping. Sam looked at the Angel with disbelief.  
“Are you sure you’re not over exaggerating?” Cas looked confused, his head tilted to the side slightly and he opened his mouth to say something; Sam cut him off. “Guess not.” He said with a breathy chuckle. “For such a ‘ladies man’ he really is bad at flirting with you.”   
The Angel perked up a bit at this. He felt a strange sensation in his chest, as if something was physically rising higher. He tried his best to control his expressions, but he couldn’t help ending up looking just the tiniest bit like a hopeful puppy.   
“Dean was flirting with me?” Once again Sam put the pieces together. When one lives with a guy like Dean for so long they learn to pick up on things like body language, Sam saw right through Cas. He smiled at this new realization.   
“Yeah, actually he’s been trying for a little over a week.” Realization pooled in the Angel’s eyes, some things Dean had said and done over the last week finally made sense.  
“Should I do something about it?”   
“Well, you could try flirting back.” Sam said in a tone that would have got a ‘go to Hell’ from Dean. Cas just looked confused; sometimes it seemed like Cas was always confused, but Sam really couldn’t blame him. Anyone would be confused if they were learning human culture for the first time. Even humans were confused by human culture, there’s just too much of it.   
“How would I do that?” Cas asked, bring completely genuine. Sam tried not to laugh. He had an idea or two.  
Sam pulled out his laptop and told the Angel to sit where he could see the screen. Sam searched for ‘pickup lines’ and the two looked through long lists of bad phrases and cheesy lines.   
About twenty minutes later, Dean returned to the little motel room. He walked in to find Cas sitting at the table by the wall fiddling with a quarter. Sam didn’t seem to be in the room.   
“Where’s Sam?”  
“We found something that he thought might be relevant to the case, he went to the library to check the records.” He wasn’t lying; they did get some work done while Dean was gone.   
“You don’t think so?”  
“No.”  
“Great.” Dean put the bags and such on little counter in the little kitchen area. He pulled out a beer and popped the lid off, leaning on the counter and taking a sip. Cas didn’t take his eyes off the quarter.  
“Uh, Dean?” Cas said without looking up.  
“Yeah?”  
The Angel spoke hesitantly. “If I were to flip this coin, what would be the chances of the head landing favorably?” It was only after he finished speaking that he looked up at Dean, who gave him a look that said he wanted to put Cas in a mental hospital. The Angel though about what he’d said, it didn’t sound right. He was sure he must have said it wrong.   
“Um... Cas wha-?”  
“Never mind.” He said quickly. Dean was going to pry but Cas was saved by Sam running in with some documents held high in his hand.   
“I was right, Come look at this!” The other two got up to see what Sam had. Dean was distracted for now and Cas had never felt so glad to be proven wrong. A few minutes later The Angel had disappeared and the Winchesters were rushing out the door. Dean hesitated for just a second as he was grabbing his coat, was Cas trying to...? No, that couldn’t be right. He was Cas, there was no way he was trying to flirt. Dean shook his head and threw on his coat, running out the door after Sam.   
******************************************************************************************************************************************************************************  
A few days later Castiel had worked up his nerve again. This time he wouldn’t mess up. Sam had ‘gotten lucky’ at the bar so Cas figured he had the whole night if he needed it, but he wouldn’t because he already knew exactly what he was going to say. He’d even practised. He recited the words to himself once more before appearing in the motel room.   
Dean was sitting on the end of one of the beds, his eyes transfixed on the television. A new episode of ‘Doctor Sexy’ was on; it was a particularly dramatic one. Dean was so focused on the programme that he didn’t notice Cas.   
“Dean, do you have a moment? I’d like to flirt with you.” He’d found that one by himself. He liked it, it got to the point.   
The only acknowledgment Dean gave was a distracted little hum; his eyes never left the screen. When no real answer came whatever courage the Angel had mustered up quickly began to fade into uncertainty. He stood there awkwardly for a bit, had Dean even realized Cas was there? He didn’t think so; maybe he should just go? No, He came here for a reason and he wasn’t going to back down just because he hadn’t been seen. He walked closer to the man on the bed.  
“Dean?” Cas said with just the tiniest touch of timidity. Dean barely glanced the Angel’s way before looking back at the television, only to whip his head back around when he realized who he’d glanced at.   
“Cas! Uh- what’s up?” Dean said, shaking himself out of his trance.   
“Nothing of importance.” The Angel said as he sat next to Dean. “What were you so focused on?”  
“a new episode of ‘Doctor Sexy’, it’s a good one too.” Dean turned his eyes back to the screen. Cas gave it a brief look and decided to focus on Dean instead. He saw the way that Dean looked at the actor Cas presumed to be Doctor Sexy; an idea popped into his head. He was speaking before he had time to think.   
“I could be your Doctor Sexy.” His tone was dead serious, there was no way to misinterpret this.   
Dean looked up at the Angel beside him, searching for any sign of... of what? Cas didn’t joke around, if he’d been put up to it then he would have at the very least sounded confused when he said it. Hell, it was a miracle he’d said it like a pickup line in the first place! So it was real. Dean had wanted this for so long, and now that it was happening he had no idea what to do. It was his turn not to think as he leaned in and captured the Angel’s lips with his own.  
It was awkward and a little rough, but passionate. Lips tangled and teeth clicked. One of Dean’s hands twisted into Cas’ short hair while the other tugged at the Angel’s hip. Cas wrapped his arms around Dean and let his stubby nails press into Dean’s shoulder blades, a little moan escaping him and sending a shiver down Dean’s spine.   
They broke for air just for a second before they were at it again, noses bumping lightly in the process. Dean’s teeth nipped lightly at Castiel’s lower lip, causing the Angel to let out a small gasp. Dean used the opportunity to slide his tongue into Cas’ mouth. Cas was a little bewildered but welcomed the new sensation of Dean’s tongue rolling eagerly over his own. The Angel realized that he’d somehow ended up on Dean’s lap; he didn’t mind.   
The next time they broke for air Dean started at Castiel’s jaw line. He left a trail of kisses all the way back and then down the neck, all the while removing Cas’ tie and unbuttoning his shirt to reveal more skin. He didn’t find what he was looking for until he got the curve just above the collarbone where Cas let out a surprised gasp of pleasure. Dean concentrated on that area, nipping a licking, extracting moans and grunts from his lover. Cas felt his pants grow tighter in around his groin, he believed Dean had once referred to this as a ‘boner’.   
After dean had finished marking his Angel he went back to kissing the life out of him. Cas was starting to pick up on the tricks; he sucked lightly on Dean’s lip and let his teeth graze over it, taunting a bit. Dean let out a low, growl –like moan and pushed Cas back onto the bed. After a bit Dean pulled away and met Castiel’s awed gaze with a little smirk that sent more blood rushing to the Angel’s groin. Dean began to unbutton the rest of the shirt, exposing more and more of the soft pale skin beneath. When he finished he sat back for a moment to admire the view and Cas saw an opportunity to get a little one-up on Dean; He sat up and gave Dean a quick, sloppy kiss. It only lasted long enough for him to shrug out of his layers of open fabric and toss them aside before he laid back down with a smile that was almost smug. Dean was impressed, Cas seemed pretty eager for a guy so clueless. He smiled slyly before bending down and letting his lips graze lightly over his love bite, giving it a little kiss before smooching his way down the Angel’s chest. He paused for a moment to tease one of the hard little nipples, earning him a breathless moan before he continued his way down; he went all the way down to the waist line of Cas’ pants which he grabbed between his teeth before coming all the way back up to give his Angel a smug little peck. In any other situation the Angel might have looked disapproving, but Cas definitely approved of that. Dean sat up briefly to get rid of his own shirt before leaning down to give his lover another proper kiss.   
Their bodies were pressed together tightly, the hot skin of their torsos mingling while tongues danced and lips were molded. Dean’s hips ground gently into Cas, their hard dicks colliding through the fabric and causing delicious friction. The Angel moaned loudly into Dean’s mouth, hips bucking up a little and causing more friction. Dean let out a startled little mewl, he hadn’t expected such an immediate reaction. Dean moved to Castiel’s neck again and ground a little harder into Cas who arched up in pure pleasure.  
“Dean...” He called out breathlessly. Dean shifted slightly, just enough so that he could reach Cas’ pants; with a little help from the Angel they got the offending garments off quickly. Dean’s hands went to his own jeans to get them off too but Cas stopped him.  
“Let me.” He said, his hands hovering so close to Dean’s length. The Winchester’s breath hitched and he nodded, allowing his lover to take his time undoing the button and zipper. Cas removed the fabrics slowly, teasing Dean with the light friction it created. A quiet moan escaped Dean as the waist band of his boxer-briefs was pulled sluggishly along his shaft.   
Once Dean was fully unclothed they took a minute to just look at each other; admire each other’s forms. They saw every little crease and scar, they saw every imperfection and they still thought each other perfect. Castiel’s eyes landed on his lover’s hard cock, his curiosity peaked. He gently ran his fingers up Dean’s length which drew a sharp gasp of pleasure from Cas’ partner. Seeing this, Cas gripped the shaft carefully and started to move his hand up and down at a hesitant pace. He sped up when Dean let out a loud moan, gaining courage. Dean was soon leaking pre-come and spouting noises and almost words. The sight was very appealing to the Angel, who never too his eyes off of his lover’s face.   
“Ah- Cas, I’m-” Dean let out a loud groan as thick white liquid shot from his shaft both his and Castiel’s stomachs. Dean was breathing hard as he bent over with one arm on either side of his Angel.   
“Alright,” Dean said breathlessly. “Now it’s my turn.” He bent down to Cas’ still hard cock, licking his lips in anticipation. He started with little licks up the shaft, earning shocked gasps and moans from his Angel lover. He licked up and down the hard length for a bit before taking Cas’ tip in his mouth and giving a light suck. The Angel groaned loudly, eyes rolling back in his head. Dean slowly started taking more and more in and Cas responded wildly. Dean was sure the people in the next room could hear, but he really didn’t care. He licked and sucked and made the Angel moan his name. Castiel’s mind was numb with pleasure, he’d never felt anything so amazing! Dean swirled his tongue around Cas’ tip and Cas arched right off the bed and cried out in pure bliss. He felt like something big was coming, but he couldn’t think of what. Whatever it was wasn’t bad, he didn’t give it much thought. Then Dean let his tongue graze the sensitive skin of the slit and the Angel was sent flying overboard, crying out loudly as he was hit with an intense wave of pure pleasure.   
Dean swallowed out of no good place to spit; it wasn’t his favorite taste in the world, but it could have been much worse. He laid beside his panting Angel and looked at him with affection, he looked dazed.   
“You alright Angel Cake?” Dean asked softly but with a bit of wry humor. Cas nodded, eyes wide and cheeks flushed.  
“That was... intense.” Cas said, still trying to catch his breath. Dean chuckled.  
“Yeah, it always is the first time, let’s just wait it out here for a while and then go get cleaned up.”   
The Angel nodded. “That sounds like the best idea.”

**Author's Note:**

> So my friend and i decided to do a porn trade; he asked for bad pickup lines and frottage so this is what happened! Hope you enjoyed it! :3


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